


Awkward First Times and Punchlines

by JellyPanda00



Category: IT (Movies - Muschietti), IT - Stephen King
Genre: Anal Sex, Awkwardness, Bad Jokes, Dorks in Love, Eddie Kaspbrak Loves Richie Tozier, First Time, Fluff and Smut, Laughter During Sex, M/M, Richie Tozier Loves Eddie Kaspbrak, Talking, Teasing
Language: English
Status: Completed
Published: 2020-03-24
Updated: 2020-03-24
Packaged: 2021-03-01 04:28:22
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,463
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23289277
Author URL: https://archiveofourown.org/users/JellyPanda00/pseuds/JellyPanda00
Summary: Richie knew he was the awkward one, but he also knew it didn’t matter with Eddie. So when they were sitting on Richie’s sofa weeks after their whispered confessions of “I love you’s” in the hospital while Eddie recovered, the last thing he expected was for the night to take such an awkward turn.
Relationships: Eddie Kaspbrak/Richie Tozier
Comments: 4
Kudos: 110





	Awkward First Times and Punchlines

**Author's Note:**

> this is literally based on a date that I had, like I came straight home and wrote this, but instead of a cute fluffy experience with someone I love, it was just weird because I was being too awkward and kept saying no. But at least I got the idea for this fic out of it ammiright? Enjoy!

Richie Tozier was king of awkward.

All his life, even as an adult, he was nothing but gangly limbs and huge glasses, weird jokes that went too far and killed the mood. At 44, he had more or less gotten it under control, or at least, learned to deal with the awkwardness that seemed to follow him like a shadow, but he was still so awkward he could damn near trademark it.

It was one of the reasons he loved Eddie Kaspbrak so much. 

Since they first met, Eddie had taken his awkwardness and ran with it, matching it so well that when they were together it faded into nonexistence. Around him, he could feel normal, like he wasn’t cursed to be weird or whatever it was that always messed him up. Remembering his childhood best friend and first love was the greatest thing to happen to him in 27 years and getting to be with him was a dream.

Richie knew he was the awkward one, but he also knew it didn’t matter with Eddie. So when they were sitting on Richie’s sofa weeks after their whispered confessions of “I love you’s” in the hospital while Eddie recovered, the last thing he expected was for the night to take such an awkward turn.

He looked so good sitting there, griping at Richie about the music he had put on to fill the silence, half drank glass of wine sloshing in his hand as he moved around to get comfortable. The scar on his cheek had healed nicely, giving him a mysterious, sexy look to his cute face that Richie adored with his whole heart. His hair was neatly combed as always, the alcohol bringing a flush to his cheeks that nearly matched his favorite red jacket that he adorned to keep off the chill of the spring night.

“Are you listening?” he asked, snapping Richie’s attention away from just how good he looked.  
“Not at all,” Richie shook his head blatantly.

Eddie glared petulantly, mouth opening to undoubtedly say something back to him when Richie leaned forward, stealing his lips in a sweet, chaste kiss.

He could feel his shoulders relaxing under his hand that rested against him, melting into the touch in an obvious sign for more. Richie obliged, body singing when his hands found his chest, resting softly against his t-shirt as he pulled him in for another kiss, opening his mouth and licking into Eddie’s.  
They had made out before, the first time being in Derry when Eddie was discharged, and the second when Eddie got his own apartment in LA, just a few blocks from Richie’s. They hadn’t quite made it past that though, not that Richie was going to push. He himself was still coming to terms with being not sexually repressed anymore, and he was sure Eddie was working through his own issues as well, but tonight felt different. Maybe it was the wine, the empty bottle still sitting on the cabinet just feet away, or the way Eddie felt so pliant against him, every move he made letting Richie know he was doing something right as he moved closer and closer until their bodies were pressed tightly together on the small couch.

Eddie sighed into his mouth, something so sweet and soft it verged on a moan and it drove Richie mad, pulse skyrocketing. He wanted to hear that sound over and over again, he would do anything for it, made a slave to the noise in a matter of seconds.

A hand made its way into his messy hair, fingers running through it with a gentle scrape of his nails against his scalp that made Richie preen. He reached down, rucking Eddie’s shirt up and running his hand over his chest, loving the way he shivered underneath him.

“Can I take your shirt off?” Richie asked breathily against his lips, leaning back just far enough he could see his reaction.  
Eddie nodded but before Richie could do so, he was pushing his own jacket off and pulling his shirt over his head, pushing them both off the couch and onto the floor in disregard. Richie watched with fascination, admiring all of the man’s muscles, the rough scar on his chest the only blemish visible on the otherwise perfect man. 

His tongue was sweet with remnants of the wine as Richie licked into his mouth, kicking off his own shoes and pushing his open Hawaiian shirt off with a little help from Eddie.

His back was starting to hurt from the crouched position, but he was alright with that because every time he opened his eyes, there was Eddie, head back against the sofa with his eyes closed shut and a dreamy smile before he blinked blurrily at him in question as to why he stopped kissing him. As he stared down at him, cupping his face to see him nuzzle into the touch, so docile and not like regular, not-kiss-drunk Eddie. He couldn’t for the life of him understand why a man like him would even want to be with Richie Trashmouth Tozier, but he thanked his lucky stars every day for the opportunity to even have him in his life again.

He grabbed hold of the loops on Eddie’s jeans, using them to pull him down to the edge of the couch so Richie could slot himself between his legs, the hardness in his pants pressed against his abdomen as he got on his knees, his own dick stiff and uncomfortable in his pants.

Richie was practically vibrating with excitement. This was by far the farthest their makeout sessions had gone, shrugging out of his t-shirt, and the prospect of taking the love of his life to his bed was riveting, electrifying to his very core. 

Eddie kept his big, brown, doe eyes locked on his every move, Richie meeting his stare with his own as he took a nipple into his mouth, sucking on the nub while he tweaked the other, making Eddie let out another half sigh-moan combination that was so soft he could barely hear it over the background music. 

Encouraged, Richie switched, sucking and nibbling at the other nipple and pressing himself down in invitation for Eddie to rut up against him which he did, a filthy grind in his hips that let Richie know he was doing a good job. Pulling off, he gave his lips a final kiss before sitting back on his heels. He reached down, picking up Eddie’s leg and grabbing his sneaker, ready to pull it off.

“No.”

His voice was weak, quiet and shaky. 

Richie froze, looking up at Eddie who had his eyes squeezed tight, one hand clenched in a fist he didn’t know he was making on his thigh.

“What’s wrong?”

Eddie looked distraught for a moment, prompting Richie to pull away completely, taking a seat next to him on the couch again back where he was when they first started.

“I don’t know,” he whimpered. “I’m sorry.”

“It’s okay, baby, don’t apologize, you don’t have anything to be sorry for,” Richie shook his head frantically, bending down to grab Eddie’s shirt and hand it to him. He accepted gratefully, pulling against himself to give a sense of modesty.

Richie leaned back in his seat, neither saying a word for a long, uncomfortable, uncertain silence that dragged on for minutes. It was probably the longest they had ever been silent in each other’s presence in their entire lives, no bickering or teasing in the thick atmosphere that could be cut with a knife.

“I’m sorry. I don’t know,” Eddie started to explain, a confused look on his face as he tried to explain what it was that he was feeling. “I just… I don’t know. I guess I got overwhelmed?”

The statement was one that was much more of a question than Eddie had meant for it to be, looking to Richie like he would hold the answer.  
“Its okay,” Richie assured him, though he felt a little at a loss for what to say. It was okay, in fact, it was more than okay. The last thing he wanted was to push him into something he didn’t want. “Everyone gets overwhelmed sometimes, Ed’s, your mom used to all the time.”  
Eddie cracked a smile, slapping Richie with his shirt. “Shut the fuck up about my mom, dumbass.”

Richie snickered, the air between them easing into something less tense, though a new awkward feeling arose in its place until it felt damn near suffocating. Eddie felt it too, reaching for his wine glass and sipping it silently. Richie followed his lead, downing his glass in several large gulps, the only thing to be heard in the room was the downright annoying music that Richie had put on.

“They shot Harambe in the head (yeah yeah yeah)

They shot Harambe now he's dead (yeah yeah yeah)”

“Jesus fucking christ,” Eddie snorted at the chorus. “What the fuck.”  
“What?” Richie’s chest shook with barely contained laughter. “You don’t appreciate my sexy music playlist?”

“No.” Eddie shook his head, laughing harder. “I don’t. Wait,” Eddie glanced at the tv where the song title and playlist was listed. “It’s actually in your sexy music playlist? I hate you,” he chuckled. “Change the damn song.”

He looked so damn beautiful when he laughed like that. It made Richie light headed every time his face lit up, especially when it was him who put the smile on his gorgeous face.

“Can I kiss you?” Richie blurted out before he could even really think about it and promptly cursed himself for it. He had jus been rejected like, five seconds ago, he had no business asking to kiss him. He quickly blundered on, trying to help himself out. “Again? If you want, if you don’t that’s fine its totally… totally great,” he gulped.

Eddie paused, considering it before nodding, letting Richie cup his cheek and draw him in once more.

Instead of pushing further as he had earlier, Richie sat back, just basking in the proximity, their knees pressed together and Eddie’s arm in his lap, hand clasped around his thigh. His erection had flagged some, but not enough that the closeness of his hand to his dick was enough to deter it from giving an excited twitch.

“Can… can I suck you off?”

Richie blinked. 

“What?”

Eddie’s face went bright red, looking away quickly. “Nothing.”

“No no no no no,” Richie shook his arm, hyper-focused on what had just come out of his mouth. “Hey, come on, Edwardo, what did you say?”

“I asked if I could suck you off, prick.” Eddie snapped, defensively.

_God, he’s so cute_ , Richie thought, awestruck.

When Richie didn’t respond fast enough, Eddie began to babble nervously. “Maybe it will help me relax? I don’t know. I don’t know why I’m being so weird about this,” Eddie ran a hand through his hair. “It’s not like I don’t want to have sex with you, I definitely do, but it’s just a lot ya know?”

Richie nodded, understandingly. “We’re 40-year-old gay men who have never had gay sex because we got amnesia from a murderous space clown and repressed it for 27 years. Its gonna be a lot, Ed’s. It’s okay. It would be okay if you want to wait too. But if you want to suck me off, I’m all for that.” Richie said enthusiastically.

“Well, now I’m not doing it.” Eddie crosses his arms like a brat, taking a sip of his wine.

Richie groaned, adjusting the thick frames that sat on his face, displaced by all the action his face had seen in the past few moments. “Really?” 

Eddie nodded, eyebrows raised. Richie groaned. “God, you’re so mean to me. I love it.”

“I love you.”

Richie’s head snapped over to look at him. He always figured he would be the first to say I love you outside of the hospital, which they both decided did not count. Nothing really counted after several near-death experiences.

“I love you too,” he whispered back, giving him a wide, toothy smile.

At least the weird air between them was gone now, the tender moment erasing the awkwardness from before.

Eddie sucked down the last of the wine in his glass, setting the empty cup down on the coffee table before standing abruptly. “Can we go to your room?”

“Are you sure?” Richie asked though he hurried to follow.

He could feel Eddie’s gaze looking him over, down his chest to his still half-hard dick tenting his pants.

“I’m sure.” His tone was dark and seductive.

Riche melted. He knew what he looked like, he wasn’t especially well defined, he had a bit of a belly and he was tall and hairy and kinda gross in his opinion, but if it did it for Eds, then he was okay with that. 

“It might be a little weird though,” Richie said, taking Eddie’s hand and leading him down the short, near non-existent hallway to his bedroom.

“Why?”

Richie flicked the lights on. “I haven’t changed the sheets since your mom was here last.”

Eddie groaned exasperatedly. “Seriously? Right now. You’re going to set me up for shitty punch lines about my mom while trying to get me into bed.”  
“Come on, Eds, you know me. I got jokes for days. I’m hilarious,” Richie walked into the room, falling onto the dark blue comforter and leaning down on his elbow, other hand on his waist. He wiggled his eyebrows at his boyfriend who let out a cute snort, shaking his head.

It gave Richie the chance to really look at Eddie, now that he had dropped his shirt somewhere along the line. He definitely worked out a lot more than Richie, he had defined muscles that promised strength despite his shorter stature and a sexy trail of hair leading down into the tops of his pants, disappearing underneath.

“Definitely a twunk.” Richie murmured.

“I don’t know what that is,” Eddie pointed at him, approaching the bed. “And I don’t want to.”

Richie laughed. He couldn’t really think of another person he had ever been with, casually or romantically, that made him laugh as much as Eddie. Likewise, Eddie couldn’t for the life of him imagine Myra who was the first and only person he ever had sex with making him laugh during such an intimate moment.

“Should I take my pants off?” Eddie asked. 

Richie felt a joke dying on his lips at the look on Eddie’s face, genuinely looking for guidance. “Yeah, if you want. I’ll take mine off too.”

Eddie bit his lip, reaching for the button on his jeans. He hesitated before looking back at Richie with trepidation. 

“I got an idea,” Richie scrambled off the bed, standing to face his boyfriend head-on. “If we’re both naked, would that make it easier?”  
Eddie nodded, though he didn’t speak, eventually kicking his shoes off.

The scrunching of fabric filled the air as they both stripped to their tighty-whities. Richie cracked, “dude I can’t believe you still wear those.”  
“So do you! You can’t make fun of me for these, you have on the same god damn brand!” Eddie cried, reaching out to grab onto the band, pulling it with a snap so it popped Richie’s hip.

“You look like a dork,” Richie shrugged. “You’re going to have to take them off.”  
“Shut,” Eddie ordered. “The fuck. Up.”

With a shove, their underwear hit the floor simultaneously, though their eyes never strayed from each other, a challenge unspoken between them as to who would look away first. As it turns out, it was Eddie, glancing down and back up, shocked. “You’re kidding me. “

Richie, slightly offended, was taken aback. “What?” was there something gross on him he didn’t know about? What was with the tone?

“You actually have a big dick.” Eddie deadpanned. “No, you can’t make all that talk about how big it is and it actually be that big.”

“Wait, so you’re mad at me because I have a big dick?” Richie choked.  
Eddie was suddenly stepping into his space, reaching up to pull Richie’s face down close enough for him to lean up in a kiss. 

There was something enchanting, enthralling at the press of his bare chest against his, the feeling of their hips brushing against each other like a wisp of wind and it set him ablaze, like a candle against a spark. He grabbed Eddie, cupping his cheeks and kissing him hungrily as if he was going to die if he didn’t get enough of him. It was hard, teeth clicking together briefly, hot and messy, leaving them both panting, spit drying to their kiss bitten lips though neither really cared.

Richie guided them both back until the bedframe hit the back of his legs. He sat down, raking his nails down the man’s sides to make him shiver. 

There it was. Eddie’s dick, half-hard and right in front of him for the first time in his life. The source of all his teenage wank sessions and even some of his adult jerk offs these past few weeks. It was more or less what he had imagined, cut and average, a tuft of brown hair at the base, looking as good as a dick could.

His mouth watered as he thought about taking him into his mouth. Instead, he ran a hand up the shaft, taking him into his hand in a few painfully slow rolls of his wrists, Eddie grabbing at his shoulders, gasping.

“You okay, spaghetti?” Richie asked quietly.

“Don’t call me that,” Eddie grumbled, a whine to his voice that took the edge out of his words.

Richie paused his movements, Eddie letting out a groan of frustration, hips giving an uncontrollable twitch, seeking out the pleasure once again. 

“I’m okay,” Eddie looked as if he was about to stomp his foot in a tantrum. “Just keep touching me.”

Richie grinned. “Okay, wanna lay down?”  
Eddie nodded.

After some quiet, awkward shuffling, they were laying down on the comforter.

Eddie’s face was beet red and Richie imagined he didn’t look much better, he could feel the heat radiating off of his face as they both looked at each other for a moment.

“Why does it feel like we’re fucking… teenagers or something about to have sex for the first time, why is it so awkward?” Eddie asked, disgruntled.

Richie shrugged, relieved Eddie brought up the weird feeling in the air that had returned once more. “No idea. Is it you or me?”

“Both?” 

They snorted simultaneously, eyes crinkled and noses scrunched in amusement. 

“I’ve only ever been with Myra. Met her in college. I don’t know what I’m doing.” Eddie explained.

“I don’t either. I mean,” Richie sat back against the pillows. He guessed if Eddie wanted to have a heart to heart right then, he might as well go in for it too. “I had sex with girls and like. Crappy handjobs in bathrooms from guys when I was blackout drunk. Guess cause it made it easier.” 

Easier than admitting he was gay. Easier than owning up to all the accusations of his childhood that came in the form of slurs hurled his way.

“So… want to just deal with the weird and maybe it’ll get less weird?” his doe eyes were turned back to Richie again, wide and earnest.

“Yeah, yeah okay, we can do that. Can… can I bottom?”

He almost expected to be told no. It was always the smaller guy in the porn that he watched that bottomed, but Eddie nodded enthusiastically. “Yeah, do you have condoms?”

Richie looked over at his bedside dresser, sitting up to grab a condom from the box he kept and the lube. 

Eddie sat up, situating his body over Richie’s, stealing him in another kiss.

It was easy to get lost in the feeling, focusing less on his hands and more on the way Eddie’s mouth felt against his. Before he knew it, his hands were in his hair, against his neck, while Eddie pushed his legs apart, settling between them and rubbing a soothing hand against his thigh.

The pop of the cap startled him out of the trance and then Eddie’s warm, slick hand was prodding against his hole, inexperienced and clumsy but enthusiastic nonetheless.

The first finger was uncomfortable but he expected it to be.

“Relax,” Eddie ordered, his voice rough as if that would help anything.

“I am relaxed!”

“You’re not relaxed, I can literally feel it.”  
Richie snorted, doing his best to relax his muscles. “Fine yeah okay, quit yelling though, I’m literally the one with something up my ass, not you.”

Eddie fucked his finger into him some, making Richie’s breath come out harshly at the movement. “I hate you.”

“I love you too, babe.”

The second finger was much more of a stretch to which Richie whined, pulling lightly at his partner’s hair.

“Good?” Eddie smirked as if he had just won a prize or something, and it was Richie’s turn to feel embarrassment rush up his spine.

“Shut up.”

Eddie ran a hand over his cock, stroking it slowly and watching his every move, the way he bit his lip and arched into the touch, rocking back onto his fingers with every move.

The third finger pushed in beside the other two, stretching him open perfectly. Richie gasped, head thrown back against the pillows, a whine choked out on every thrust.

“Eds Eds Eds please,” he gasped, every inch of his body on fire with pleasure.

“Ready?” Eddie asked uncertainly to which Richie nodded, eyes squeezed shut to get some semblance of control back.

There was a tale-tale ripping of foil, opening his eyes in time to see Eddie roll the condom over his cock, stroking himself slowly, eyes never straying from Richie’s face.

“It’s not polite to stare, Spaghetti,” Richie teased.

“Don’t care,” Eddie stated, leaning over him for another kiss.

Richie held him close, gripping his lover’s shoulders, feeling the way his muscles moved as he reached between them, guiding his cock up. The first touch of the head was like electricity and Richie could help but think _holy shit I’m finally having sex with Eddie Kaspbrak maybe there is a god._

His cock was thick, stretching him wide until tears prickled are the corners of his eyes as he pushed inside to the hilt. He pushed his glasses up his forehead and kissed at the tears. “Did I hurt you?”

“No. Kinda. No.”

“What does that mean?” Eddie asked worriedly.

“You’re so fucking thick. Like thicc. Two c’s.”

“Shut the fuck up Richie,” Eds snorted, nose scrunched and face full off adoration.

“Just give me a second okay?” Richie asked softly.

Eddie nodded. 

Richie gave an experimental wiggle of his hips, pleased with the groan it ripped from Eddie’s chest. 

“Why are you so tight Jesus Christ,” he whined, hand on Richie’s hip tightening until his fingertips dug into the flesh bruisingly.

“Fuck me.”

Eddie didn’t waste time, thrusting in slow and hard, too gentle for Richie. He tried to force his hips down, make him go faster but Eddie held him down with an evil grin.

“Eds com’on,” Richie whined. Eddie didn’t give in, continuing his slow methodical movements.

How did he miss how strong the man was? Eddie was small, compact, but he worked out and Richie could literally feel it, every push he tried to give was held down by his strong hands, unyielding strength. 

Richie ached at every touch, every caress; like a deep full-body shiver was compressed at the base of his spine looking for a way out. He used his legs to encircle Eddie’s waist, drawing him in.

“Holy shit Eds, please!”  
Eddie’s mouth was back on his neck, biting at the reddened skinned and sucking harsh marks everywhere he could reach. “Again.”

“What?” Richie cried.

“Beg again,” he growled.  
What kind of wet dream was this from? Did he fall asleep without realizing it?

“Where did you get that from?” Richie panted wildly.

Eddie pulled back, doe eyes wide. “Too much? Too weird?”

“Too much? Babe, you’re gonna kill me,” Richie adjusted his glasses that had been knocked askew. “That was the hottest thing I’ve ever heard in my life, don’t stop.”

“Oh. Cool.”

Richie stared, dumbfounded. “Cool? Cool? I’m getting my brains dicked out and you’re… I love you so much.”

Eddie grinned, leaning back down to continue biting his neck and collarbone, pounding into him harder. “Well, are you going to beg for me, baby?” he cooed softly.

“Fuck, fuck yes, please go harder, please,” Richie sought purchase on his shoulders, anything that could anchor him down to the earth.

A new angle caught his prostate dead-on, making Richie sob, overwhelmed. “There, there please don’t stop.”

Eddie, assured he was doing good, pounded into him harder, hand blindly reaching for his cock that sat hard, red and leaking against his stomach. Fisting his throbbing erection, he stroked in time with his thrusts, sending Richie reeling.

“I-I,” Richie tried to form a sentence, speechless for the first time in his life. He clawed at Eddie’s shoulders and back, tears leaking at the corner of his eyes from the blinding pressure.

His body thrashed, seizing up in a tight ball of nerves, the pressure in his groin exploding.

Eddie stroked him through it in the same, inexperienced, perfect way as sparks shot through every inch of his body.

Richie finally remembered to breathe, watching Eddie’s face as he reached his own climax. His o-face was rediculous and beautiful and everything Richie had ever hoped to see, his jaw dropped and cute nose scrunched up, every inch of him stiff as a board.

Finally, his body unlocked after what seemed like hours but was only seconds, flopping down onto the bed next to Richie and pulling the condom off, tying it and tossing it into the trashcan next to the bed.

They stared up at the ceiling, reveling in the blissful aftermath.

“Was that okay?” Eddie asked quietly, breaking the silence that was previously filled with their panting breaths.

“Fantastic, spaghetti-man,” Richie breathed.

“Really?”

Richie looked over at him, surprised to see the same uncertain look on his features. “Yeah, baby, it was perfect. You know, once it wasn’t awkward. You okay?”

Eddie smiled softly, content. “Yeah. It was really weird earlier though, I’m sorry.”

“Nah, nothing to be sorry for, Eddie babe.”

“Eddie babe?” Eddie chuckled. “What is that?”

“It’s cute,” Richie grinned madly, leaning in for a kiss. “Like you.”

Eddie scooted closer so their overheated bodies overlapped, the sheets sticking to their skin with every move they made, cuddling into each other despite the heat.

**Author's Note:**

> Let me know what you thought and come talk to me on Twitter! @Jellypanda00


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